602-60-8

Usage

Uses

Used in Photodynamic Therapy (PDT):
9-NITROANTHRACENE is used as a precursor for anthraquinones, which are employed as photosensitizers in PDT. The application reason is that these anthraquinones can effectively absorb light and generate reactive oxygen species, leading to the destruction of cancerous cells upon light activation.
Used in Pharmaceutical Industry:
9-NITROANTHRACENE is used as a starting material for the synthesis of various drugs, such as Emodin (E523000), Aloe-emodin (A575400), and Rufgallol. The application reason is that these drugs have demonstrated potential therapeutic effects in treating different health conditions, including cancer.
Used in Cancer Therapy:
9-NITROANTHRACENE has potential applications in cancer therapy due to its role in the production of anthraquinones, which can be utilized in PDT and the development of anticancer drugs. The application reason is that these anthraquinones and derived drugs can target and eliminate cancer cells, offering a promising avenue for cancer treatment.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Aromatic nitro compounds, such as 9-NITROANTHRACENE, range from slight to strong oxidizing agents. If mixed with reducing agents, including hydrides, sulfides and nitrides, they may begin a vigorous reaction that culminates in a detonation. The aromatic nitro compounds may explode in the presence of a base such as sodium hydroxide or potassium hydroxide even in the presence of water or organic solvents. The explosive tendencies of aromatic nitro compounds are increased by the presence of multiple nitro groups. 9-NITROANTHRACENE may be sensitive to prolonged exposure to light.

Health Hazard

ACUTE/CHRONIC HAZARDS: 9-NITROANTHRACENE may cause skin irritation on contact.

Fire Hazard

Flash point data are not available for 9-NITROANTHRACENE, but 9-NITROANTHRACENE is probably combustible.

Purification Methods

Purify it by recrystallisation from EtOH or MeOH. Further purify it also by sublimation or TLC. [Beilstein 5 H 666, 5 II 578, 5 III 2136, 5 IV 2296.]

InChI:InChI=1/C14H9NO2/c16-15(17)14-7-3-6-12-8-10-4-1-2-5-11(10)9-13(12)14/h1-9H

Upstream product

• 110-86-1 pyridine 
• 64-17-5 ethanol 
• 73621-46-2 9,10-dihydro-9,10-dinitroanthracene 
• 84305-14-6 9-ethoxy-10-nitro-9,10-dihydroanthracene 
• 84305-13-5 9-methoxy-10-nitro-9,10-dihydroanthracene 
• 33685-60-8 9,10-dinitroanthracene 
• 120-12-7 anthracene 
• 67-66-3 chloroform 
• 10544-72-6 dinitrogen tetraoxide 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 7697-37-2 nitric acid 
• 98-95-3 nitrobenzene 
• 7664-41-7 ammonia 

Downstream Products

• 90-44-8 anthracen-9(10H)-one 
• 523-27-3 9,10-Dibromoanthracene 
• 84-65-1 9,10-phenanthrenequinone 
• 629-45-8 dibutyl disulfide 
• 74851-71-1 aci-9,9'-dinitro-10,10'-dihydro-10,10'-bianthryl 
• 98-46-4 3-trifluoromethylnitrobenzene 
• 150-60-7 dibenzyl disulphide 
• 1210-12-4 9-cyanoanthracene 
• 10496-15-8 dihexyl disulfide 
• 642-31-9 9-anthracene aldehyde 
• 529-86-2 9-anthrol 
• 434-84-4 bianthronyl 
• 716-53-0 9-chloroanthracene 
• 14789-48-1 bromo-9 nitro-10 anthracene 

Relevant academic research and scientific papers

SELECTIVE OXIDATION OF ANTHRACENE TO ANTHRAQUINONE IN ACETIC ACID WITH AIR IN PRESENCE OF NITRIC ACID

The oxidation of anthracene in acetic acid with air in the presence of small proportion of nitric acid produced high quality anthraquinone with acceptable yields.A possible mechanism is suggested which explains the predominance of the oxidation reaction compared with that of nitration.

Reaction of Polycylic Aromatic Hydrocarbons (PAH) with Nitrogen Dioxide in Solution. Support for an Electron-Transfer Mechanism of Aromatic Nitration Based on Correlations Using Simple Molecular Orbital Theory

Eight unsubstituted, polycyclic aromatic hydrocarbons (PAH) were allowed to react with nitrogen dioxide in dichlormethane at 25 deg C, and relative rate constants were obtained by direct competition techniques.The rate constants depend markedly on substrate structure, with over a 104 difference in rate constants between the least reactive (benzene) and most reactive (perylene) compounds studied.The major products formed from most substrates are nitroaromatics.Anthracene, however, also reacts with nitrogen dioxide to form appreciable amounts of 9,10-anthraquinone.Linear free energy relationships were determined between rate data and molecular orbital parameters based on models involving rate-determining ?-complex formation or electron-transfer (ET) reactions.Based on the better correlations obtained using the latter model, it is suggested that the more easily ionized PAH undergo nitration by an ET mechanism.Values of absolute rate constants for the nitration of three of the PAH (as measured by stopped-flow) also are reported and correlate well with our relative rate constants.The formation of 9,10-anthraquinone is suggested to result from the trapping of the intermediate anthracene radical-cation by water.

Tetranitroethylene. In Situ Formation and Diels-Alder Reactions

The reaction of hexanitroethane with dienes gave the Diels-Alder adducts of tetranitroethylene.Thus, the reaction in refluxing benzene of hexanitroethane with anthracene gave 11,11,12,12-tetranitro-9,10-dihydro-9,10-ethanoanthracene.Similarly, 9-methylanthracene and 9,10-dimethylanthracene gave 9-methyl-11,11,12,12-tetranitro-9,10-dihydro-9,10-ethanoanthracene and 9,10-dimethyl-11,11,12,12-tetranitro-9,10-dihydro-9,10-ethanoanthracene, respectively.Cyclopentadiene reacted with hexanitroethane in methylene chloride at -10 deg C to give 5,5,6,6-tetranitro-2-norbornene.Reaction of the anthracene adduct of tetranitroethylene with sodium iodide gave the sodium salt of 12-nitro-9,10-dihydro-9,10-ethanoanthracen-11-one, which was protonated with acetic acid to give the corresponding nitro ketone.Treatment of the sodium salt with clorine and bromine gave 12-chloro-12-nitro-9,10-dihydro-9,10-ethanoanthracen-11-one and 12-bromo-12-nitro-9,10-dihydro-9,10-ethanoanthracen-11-one, respectively.

Novel aromatic-polyamine conjugates as cholinesterase inhibitors with notable selectivity toward butyrylcholinesterase

Three types of aromatic-polyamine conjugates (6a-6s) were designed, synthesized and evaluated as potential inhibitors for cholinesterases (ChEs). The results showed that anthraquinone-polyamine conjugates (AQPCs) exhibited the most potent acetylcholinesterase (AChE) inhibitory activity with IC 50 values from 1.50 to 11.13 μM. Anthracene-polyamine conjugates (APCs) showed a surprising selectivity (from 76- to 3125-fold) and were most potent at inhibiting butyrylcholinesterase (BChE), with IC50 values from 0.016 to 0.657 μM. A Lineweaver-Burk plot and molecular modeling studies indicated that the representative compounds, 6l and 6k, targeted both the catalytic active site (CAS) and the peripheral anionic site (PAS) of ChEs. Furthermore, APCs did not affect HepG2 cell viability at the concentration of 100 μM. Consequently, these polyamine conjugates could be thoroughly and systematically studied for the treatment of AD.

2-Methyl-1,3-disulfoimidazolium polyoxometalate hybrid catalytic systems as equivalent safer alternatives to concentrated sulfuric acid in nitration of aromatic compounds

Ionic liquid-derived polyoxometalate salts [mdsim]3[PM12O40] (where M?=?W and Mo) of two heteropolyacids H3PW12O40.nH2O and H3PMo12O40.nH2O were synthesized using 2-methyl-1,3-disulfoimidazolium chloride ([mdsim][Cl]) ionic liquid and the corresponding heteropolyacids. Three equivalents of [mdsim][Cl] were treated with the respective Keggin-structured heteropolyacids (one equivalent) in aqueous medium at room temperature to afford the water-stable ionic polyoxometalates as acidic solids. They were completely characterized using spectroscopic and other analytical techniques including thermal analysis and Hammett acidity studies. The inherent Br?nsted acidic properties of ─SO3H group of these polyoxometalate salts were studied for the nitration of aromatic compounds with 69% HNO3 at normal temperature and 80°C without use of any external concentrated sulfuric acid. These strongly acidic polyoxometalates display good recyclability and efficient reusability.

Nitration of arenes by 1-sulfopyridinium nitrate as an ionic liquid and reagent by in situ generation of NO2

1-Sulfopyridinium nitrate was synthesized as a potent nitrating agent for the nitration of arenes without the need for any co-catalysts. A variety of nitro compounds were synthesized and fully characterized by IR, 1H NMR, 13C NMR, thermal gravimetric analysis (TGA), differential thermal gravimetry (DTG), CHN analysis and mass spectroscopy. Mechanistically, in situ generated nitrogen dioxide as a radical from the reagent is proposed for the presented nitration protocol.

Synthesis of new chiral 1,3-aminoalcohols derived from levoglucosenone and their application in asymmetric alkylations

We have developed a simple procedure for the preparation of chiral 1,3-aminoalcohols using the biomass derivative levoglucosenone, as the chiral starting material. 1,3-aminoalcohols, bearing primary and tertiary amino groups, were tested as chiral catalysts in the asymmetric addition of diethyl zinc to benzaldehyde.

Phosphoric acid modified montmorillonite clay: A new heterogeneous catalyst for nitration of arenes

The easily available montmorillonite clay is treated with phosphoric acid and 10 wt.% is found to be the optimum concentration of phosphoric acid that can be adsorbed chemically on the surface of the clay. Acidity of this phosphoric acid treated montmorillonite clay (PAM) is determined by volumetric as well as potentiometric titration and characterized. Catalytic efficacy of PAM in nitration of various aromatic compounds is reported.

Design of ionic liquid 3-methyl-1-sulfonic acid imidazolium nitrate as reagent for the nitration of aromatic compounds by in situ generation of NO 2 in acidic media

3-Methyl-1-sulfonic acid imidazolium nitrate ([Msim]NO3) as a new Bronsted acidic ionic liquid and nitrating agent was prepared and used for the efficient nitration of aromatic compounds (even aniline derivatives). The dramatic effect of this reagent by in situ generation of nitrogen dioxide as a radical on aromatic compounds to give nitroarenes has been studied.

Nitration of aromatic compounds under neutral conditions using the Ph 2PCl/I2/AgNO3 reagent system

Aromatic compounds were nitrated efficiently under essentially neutral conditions by employing Ph2PCl in the presence of I2 and AgNO3. This method minimizes waste products compared to traditional methods and gives the corresponding mononitro derivatives in good to excellent yields in dichloromethane at room temperature.